Paul Krassner began publishing a small-circulation magazine called The Realist in New York City in 1958 because he believed there existed excessive restraints on speech in American culture. The publication began with a combination of earnest critiques and good-humored satires on such topics as organized religion, sexual mores, Cold War paranoia, and civil rights. By the mid-sixties, the magazine was enlarging the space not just for what opinions could be expressed but also for the way those opinions were expressed and, in the process, testing the boundaries of obscenity. As Krassner became a bitter opponent of the Vietnam War and the administration that waged it, he combined vulgarity and protest into a startling form of self-expression that, ultimately, resulted in the magazine’s best-remembered piece. Issues of The Realist from 1968 demonstrate that Krassner flirted with political radicalism, particularly in that heady year, but ultimately, his war was with the cultural censors. The humor in The Realist, both bold and sophomoric, led to denunciations from journalists, politicians, and feminists. The condemnation of the latter group particularly stung the usually thick-skinned editor, who had long made the case for equal pay and reproductive rights for women. The Realist is the principal example of a 1960s publication – and, by mid-decade, a widely read one – that reveled in psychedelic and sexual experimentation, condemned what it considered evil, but above all, considered the right to self-expression the most essential American value.